Download - metal-organic compoundsjournals.iucr.org/e/issues/2010/05/00/bq2206/bq2206.pdf · Muhammad Danish, Iram Saleem, M. Nawaz Tahir, Nazir Ahmad and Abdur Rauf Raza S1. Comment In continuation

Tetrakis(l-2-methylbenzoato-j2O:O000)-bis[(methanol-jO)copper(II)]

Muhammad Danish,a Iram Saleem,a M. Nawaz Tahir,b*

Nazir Ahmada and Abdur Rauf Razaa

aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, andbDepartment of Physics, University of Sargodha, Sargodha, Pakistan

Correspondence e-mail: [email protected]

Received 7 April 2010; accepted 10 April 2010

Key indicators: single-crystal X-ray study; T = 296 K; mean �(C–C) = 0.005 A;

R factor = 0.043; wR factor = 0.098; data-to-parameter ratio = 19.3.

In the title compound, [Cu2(C8H7O2)4(CH3OH)2], the Cu—O

bond distances are in the range 1.943 (2)–2.149 (2) A within a

sligthly distorted square-pyramidal coordination. The

Cu� � �Cu separation is 2.5912 (4) A. In the crystal, the

molecules are linked into polymeric chains propagating in

[001] by intermolecular O—H� � �O hydrogen bonds and C—

H� � �� interactions.

Related literature

For our work on the synthesis of various metal complexes of 2-

methylbenzoic acid, see: Danish et al. (2010). For related

structures, see: Kabbani et al. (2004); Rao et al. (1983); Sunil et

al. (2008); Xin & Liu (2008).=

Experimental

Crystal data

[Cu2(C8H7O2)4(CH4O)2]Mr = 731.71Triclinic, P1a = 10.7474 (9) Ab = 12.1403 (11) Ac = 14.1709 (11) A� = 113.805 (2)�

� = 91.096 (3)�

� = 93.238 (3)�

V = 1687.2 (2) A3

Z = 2Mo K� radiation� = 1.32 mm�1

T = 296 K0.30 � 0.14 � 0.08 mm

Data collection

Bruker Kappa APEXII CCDdiffractometer

Absorption correction: multi-scan(SADABS; Bruker, 2005)Tmin = 0.804, Tmax = 0.898

27787 measured reflections8232 independent reflections5004 reflections with I > 2�(I)Rint = 0.047

Refinement

R[F 2 > 2�(F 2)] = 0.043wR(F 2) = 0.098S = 1.028232 reflections427 parameters

H atoms treated by a mixture ofindependent and constrainedrefinement

��max = 0.30 e A�3

��min = �0.31 e A�3

Table 1Hydrogen-bond geometry (A, �).

Cg1 and Cg2 are the centroids of C2–C7 and C28–C33 rings, respectively.

D—H� � �A D—H H� � �A D� � �A D—H� � �A

O5—H5A� � �O7i 0.70 (3) 2.11 (3) 2.793 (3) 167 (4)O6—H6A� � �O2ii 0.72 (3) 2.10 (3) 2.812 (2) 174 (4)C18—H18A� � �Cg1ii 0.96 2.98 3.749 (4) 137.00C23—H23� � �Cg1iii 0.93 2.87 3.735 (4) 154.00C13—H13� � �Cg2iv 0.93 2.97 3.877 (4) 165.00

Symmetry codes: (i) �xþ 1;�y;�z; (ii) �xþ 1;�y;�zþ 1; (iii) �xþ 1;�y� 1;�z;(iv) �xþ 1;�yþ 1;�zþ 1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT

(Bruker, 2007); data reduction: SAINT; program(s) used to solve

structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine

structure: SHELXL97 (Sheldrick, 2008); molecular graphics:

ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009);

software used to prepare material for publication: WinGX (Farrugia,

1999) and PLATON.

The authors acknowledge the provision of funds for the

purchase of diffractometer and encouragement by Dr

Muhammad Akram Chaudhary, Vice Chancellor, University

of Sargodha. The authors also acknowledge the technical

support provided by Bana International, Karachi, Pakistan.

Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: BQ2206).

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,

USA.Danish, M., Saleem, I., Ahmad, N., Raza, A. R., Starosta, W. & Leciejewicz, J.

(2010). Acta Cryst. E66, m459–m460.Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.Kabbani, A. T., Zaworotko, M. J., Abourahma, H., Walsh, R. D. B. &

Hammud, H. H. (2004). J. Chem. Crystallogr. 34, 749–756.Rao, V. M., Sathyanarayana, D. N. & Manohar, H. (1983). J. Chem. Soc. Dalton

Trans. pp. 2167–2173.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.Sunil, A. C., Bezuidenhoudt, B. C. B. & Janse van Rensburg, J. M. (2008). Acta

Cryst. E64, m553–m554.Xin, C.-W. & Liu, F.-C. (2008). Acta Cryst. E64, m1589.

metal-organic compounds

m528 Danish et al. doi:10.1107/S1600536810013322 Acta Cryst. (2010). E66, m528

Acta Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

http://scripts.iucr.org/cgi-bin/cr.cgi?rm=pdfbb&cnor=bq2206&bbid=BB1
















http://crossmark.crossref.org/dialog/?doi=10.1107/S1600536810013322&domain=pdf&date_stamp=2010-04-17

supporting information

sup-1Acta Cryst. (2010). E66, m528


Acta Cryst. (2010). E66, m528 [https://doi.org/10.1107/S1600536810013322]

Tetrakis(µ-2-methylbenzoato-κ2O:O′)bis[(methanol-κO)copper(II)]

Muhammad Danish, Iram Saleem, M. Nawaz Tahir, Nazir Ahmad and Abdur Rauf Raza

S1. Comment

In continuation to synthesize various metal complexes of 2-methylbenzoic acid (Danish et al., 2010), the title compound

(I) (Fig. 1) is being reported here.

The crystal structure of (II) Tetrakis(µ-2-methylbenzoato-O,O′) -bis(2-methylbenzoic acid-O)-di-copper(ii) (Sunil et al.,

2008) has been reported. The title compound (I) differs from (II) due to the bonding of methanol at apical positions

instead of o-toluic acid. The crystal structures of (III) Tetrakis(µ-2-anilinobenzoato)-bis(methanol-copper(ii)) (Xin & Liu,

2008), (IV) Tetrakis(µ-4-chloro-3-nitrobenzoato)-bis(methanol)-di-copper(ii) (Kabbani et al., 2004) and (V) Tetrakis(µ-

acetato)-bis(methanol)-di-copper(ii) (Rao et al., 1983) have also been reported which have similar environments around

Cu-atoms as in (I).

Although the space group is centrosymmetric but the molecules of (I) are not centrosymmetric. The C-atoms of 2-

methylbenzoato A (C1—C8), B (C9—C16), C (C19—C26) and D (C27—C34) are planar with maximum r. m. s.

deviations of 0.0148, 0.0278, 0.0111 & 0.0127 Å respectively, from the mean square planes. The carboxylato groups E

(O1/C1/O2), F (O3/C9/O4), G (O7/C19/O8) and H (O9/C27/O10) are of course planar. The dihedral angle between A/E,

B/F, C/G and D/H is 35.01 (23), 40.19 (20), 36.09 (25) and 27.16 (33)° respectively. The oppositely bonded 2-methyl-

benzoato groups with Cu-atoms make dihedral angles A/C 75.77 (7)° and B/D 86.29 (7)° which confirms that asymmetric

units cannot be centrosymmetric. The coordination of Cu–O bond distances range 1.943 (2)–2.149 (2) Å [Table 1] and

the separation between Cu to Cu is 2.5912 (4) Å. The molecules are stabilized in the form of polymeric chains due to

intermolecular H-bondings and C–H···π interactions (Table 2, Fig. 2).

S2. Experimental

The sodium salt of 2-methylbenzoic acid (1 g, 6.32 mmol) was dissolved in 20 ml distilled water. Cu2So4.5H2O (0.789 g,

3.16 mmol) was separately dissolved in 20 ml distilled water. The former solution was slowly added to the later under

continuous stirring with the formation of greenish precipitates. The reaction mixture was refluxed for 3 h and cooled to

room temperature. The residue of filtration was crystallized in methanol:water (1:1). Green plate like crystals were

obtained after 48 h.

S3. Refinement

The coordinates of H5A and H6A were refined. The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and

refined as riding with Uiso(H) = xUeq(C, O), where x = 1.2 for aryl & hydroxy and 1.5 for methyl H-atoms.



Figure 1

View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability

level.

Figure 2

The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric sheets due to the intermolecular

H-bondings.



Tetrakis(µ-2-methylbenzoato-κ2O:O′)bis[(methanol- κO)copper(II)]

Crystal data

[Cu2(C8H7O2)4(CH4O)2]Mr = 731.71Triclinic, P1Hall symbol: -P 1a = 10.7474 (9) Åb = 12.1403 (11) Åc = 14.1709 (11) Åα = 113.805 (2)°β = 91.096 (3)°γ = 93.238 (3)°V = 1687.2 (2) Å3

Z = 2F(000) = 756Dx = 1.440 Mg m−3

Mo Kα radiation, λ = 0.71073 ÅCell parameters from 5004 reflectionsθ = 1.9–28.3°µ = 1.32 mm−1

T = 296 KPlate, green0.30 × 0.14 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Radiation source: fine-focus sealed tubeGraphite monochromatorDetector resolution: 7.40 pixels mm-1

ω scansAbsorption correction: multi-scan

(SADABS; Bruker, 2005)Tmin = 0.804, Tmax = 0.898

27787 measured reflections8232 independent reflections5004 reflections with I > 2σ(I)Rint = 0.047θmax = 28.3°, θmin = 1.9°h = −14→14k = −15→16l = −18→16

Refinement

Refinement on F2

Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.043wR(F2) = 0.098S = 1.028232 reflections427 parameters0 restraintsPrimary atom site location: structure-invariant

direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2(Fo2) + (0.0377P)2]

where P = (Fo2 + 2Fc

2)/3(Δ/σ)max = 0.001Δρmax = 0.30 e Å−3

Δρmin = −0.31 e Å−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion anglesRefinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq

Cu1 0.46596 (3) 0.03113 (3) 0.18544 (2) 0.0408 (1)Cu2 0.58723 (3) −0.00162 (3) 0.33076 (2) 0.0375 (1)O1 0.33402 (17) −0.07793 (17) 0.20094 (13) 0.0491 (7)



O2 0.42139 (16) −0.07056 (17) 0.34848 (12) 0.0455 (6)O3 0.40272 (17) 0.16577 (17) 0.30278 (13) 0.0491 (7)O4 0.53752 (17) 0.15696 (16) 0.42153 (12) 0.0455 (7)O5 0.3622 (2) 0.0618 (2) 0.06817 (14) 0.0594 (8)O6 0.68139 (18) −0.02251 (19) 0.45600 (13) 0.0480 (7)O7 0.54674 (17) −0.11478 (16) 0.09317 (12) 0.0457 (6)O8 0.61682 (17) −0.15929 (16) 0.22255 (12) 0.0475 (7)O9 0.61515 (18) 0.12928 (17) 0.18536 (14) 0.0519 (8)O10 0.73055 (16) 0.07076 (18) 0.28750 (14) 0.0498 (7)C1 0.3345 (3) −0.1038 (3) 0.27850 (19) 0.0434 (10)C2 0.2270 (3) −0.1791 (3) 0.29092 (18) 0.0456 (10)C3 0.1056 (3) −0.1725 (3) 0.2599 (2) 0.0603 (11)C4 0.0122 (3) −0.2479 (4) 0.2774 (3) 0.0803 (14)C5 0.0399 (4) −0.3253 (4) 0.3202 (3) 0.0863 (17)C6 0.1585 (4) −0.3326 (3) 0.3493 (3) 0.0762 (16)C7 0.2525 (3) −0.2584 (3) 0.3367 (2) 0.0558 (11)C8 0.0690 (3) −0.0852 (4) 0.2159 (3) 0.0924 (18)C9 0.4503 (3) 0.2038 (2) 0.39346 (19) 0.0415 (9)C10 0.3955 (2) 0.3091 (3) 0.4757 (2) 0.0425 (9)C11 0.3564 (3) 0.4071 (3) 0.4575 (2) 0.0531 (11)C12 0.3038 (3) 0.4971 (3) 0.5388 (3) 0.0734 (12)C13 0.2873 (3) 0.4904 (3) 0.6324 (3) 0.0799 (16)C14 0.3276 (3) 0.3954 (3) 0.6496 (2) 0.0668 (11)C15 0.3833 (3) 0.3061 (3) 0.5714 (2) 0.0533 (11)C16 0.3751 (3) 0.4205 (3) 0.3569 (2) 0.0694 (12)C17 0.2436 (3) 0.1088 (3) 0.0821 (3) 0.0784 (14)C18 0.8080 (3) −0.0418 (3) 0.4644 (3) 0.0784 (14)C19 0.5962 (2) −0.1844 (3) 0.12745 (18) 0.0411 (9)C20 0.6378 (3) −0.3025 (3) 0.05359 (19) 0.0426 (9)C21 0.5751 (3) −0.3735 (3) −0.0404 (2) 0.0530 (11)C22 0.6264 (4) −0.4802 (3) −0.1010 (2) 0.0758 (13)C23 0.7336 (4) −0.5161 (3) −0.0737 (3) 0.0876 (18)C24 0.7955 (4) −0.4456 (3) 0.0187 (3) 0.0889 (17)C25 0.7459 (3) −0.3403 (3) 0.0815 (2) 0.0686 (11)C26 0.4549 (3) −0.3410 (3) −0.0754 (2) 0.0814 (16)C27 0.7166 (3) 0.1278 (3) 0.2308 (2) 0.0465 (10)C28 0.8269 (3) 0.1984 (3) 0.2150 (2) 0.0500 (11)C29 0.9268 (3) 0.2476 (3) 0.2875 (3) 0.0651 (12)C30 1.0209 (3) 0.3152 (3) 0.2657 (3) 0.0907 (18)C31 1.0204 (4) 0.3331 (4) 0.1767 (4) 0.0993 (19)C32 0.9236 (4) 0.2825 (4) 0.1051 (3) 0.0873 (17)C33 0.8266 (3) 0.2161 (3) 0.1243 (3) 0.0690 (12)C34 0.9365 (3) 0.2357 (4) 0.3889 (3) 0.0965 (19)H4 −0.07050 −0.24412 0.25903 0.0966*H5 −0.02370 −0.37447 0.32978 0.1035*H5A 0.387 (3) 0.065 (3) 0.024 (2) 0.0713*H6 0.17652 −0.38726 0.37758 0.0911*H6A 0.654 (3) 0.005 (3) 0.505 (2) 0.0576*



H7 0.33377 −0.26120 0.35883 0.0670*H8A 0.09672 −0.11072 0.14671 0.1379*H8B 0.10695 −0.00639 0.25763 0.1379*H8C −0.02007 −0.08249 0.21503 0.1379*H12 0.27881 0.56437 0.52971 0.0880*H13 0.24844 0.55104 0.68415 0.0959*H14 0.31764 0.39110 0.71309 0.0798*H15 0.41343 0.24222 0.58320 0.0639*H16A 0.37026 0.50353 0.36801 0.1038*H16B 0.31144 0.37174 0.30660 0.1038*H16C 0.45559 0.39470 0.33218 0.1038*H17A 0.20305 0.09234 0.13523 0.1172*H17B 0.19406 0.07159 0.01864 0.1172*H17C 0.25292 0.19441 0.10173 0.1172*H18A 0.85558 0.03454 0.49473 0.1179*H18B 0.83704 −0.08773 0.39700 0.1179*H18C 0.81790 −0.08536 0.50718 0.1179*H22 0.58535 −0.52973 −0.16344 0.0910*H23 0.76504 −0.58800 −0.11737 0.1052*H24 0.86927 −0.46871 0.03826 0.1070*H25 0.78647 −0.29294 0.14474 0.0825*H26A 0.40631 −0.41338 −0.11865 0.1221*H26B 0.47288 −0.29272 −0.11359 0.1221*H26C 0.40881 −0.29619 −0.01627 0.1221*H30 1.08722 0.34991 0.31370 0.1087*H31 1.08520 0.37933 0.16478 0.1188*H32 0.92324 0.29288 0.04354 0.1050*H33 0.76043 0.18283 0.07590 0.0826*H34A 0.99931 0.29385 0.43328 0.1448*H34B 0.95867 0.15587 0.37725 0.1448*H34C 0.85763 0.24976 0.42093 0.1448*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

Cu1 0.0499 (2) 0.0448 (2) 0.0270 (2) 0.0077 (2) 0.0030 (1) 0.0133 (2)Cu2 0.0442 (2) 0.0408 (2) 0.0248 (2) 0.0041 (2) 0.0020 (1) 0.0104 (2)O1 0.0550 (12) 0.0557 (14) 0.0322 (9) −0.0021 (10) −0.0024 (9) 0.0141 (10)O2 0.0463 (11) 0.0563 (13) 0.0301 (9) −0.0044 (9) −0.0017 (8) 0.0149 (9)O3 0.0596 (12) 0.0473 (13) 0.0354 (10) 0.0151 (10) 0.0025 (9) 0.0101 (9)O4 0.0522 (12) 0.0411 (12) 0.0350 (10) 0.0080 (9) −0.0018 (8) 0.0066 (9)O5 0.0662 (14) 0.0818 (17) 0.0404 (12) 0.0200 (12) 0.0083 (10) 0.0331 (12)O6 0.0541 (13) 0.0587 (14) 0.0286 (10) 0.0147 (10) 0.0019 (9) 0.0135 (10)O7 0.0634 (12) 0.0453 (12) 0.0285 (9) 0.0133 (10) 0.0071 (9) 0.0135 (9)O8 0.0696 (13) 0.0420 (12) 0.0276 (9) 0.0116 (10) 0.0033 (9) 0.0096 (9)O9 0.0546 (13) 0.0535 (14) 0.0531 (12) 0.0057 (10) 0.0060 (10) 0.0270 (11)O10 0.0459 (11) 0.0567 (14) 0.0509 (11) 0.0039 (10) 0.0076 (9) 0.0258 (11)C1 0.0482 (17) 0.0451 (19) 0.0301 (14) 0.0040 (14) 0.0045 (13) 0.0079 (14)



C2 0.0458 (18) 0.0491 (19) 0.0287 (13) −0.0008 (14) 0.0008 (12) 0.0027 (14)C3 0.056 (2) 0.070 (2) 0.0434 (17) 0.0019 (18) −0.0024 (15) 0.0117 (17)C4 0.048 (2) 0.108 (3) 0.070 (2) −0.015 (2) −0.0107 (18) 0.024 (2)C5 0.069 (3) 0.097 (3) 0.081 (3) −0.021 (2) 0.006 (2) 0.027 (3)C6 0.089 (3) 0.063 (3) 0.073 (2) −0.007 (2) 0.012 (2) 0.025 (2)C7 0.061 (2) 0.052 (2) 0.0481 (17) −0.0054 (17) 0.0063 (15) 0.0149 (16)C8 0.065 (2) 0.122 (4) 0.094 (3) 0.017 (2) −0.009 (2) 0.047 (3)C9 0.0457 (17) 0.0377 (18) 0.0358 (14) −0.0018 (14) 0.0059 (13) 0.0100 (14)C10 0.0432 (16) 0.0363 (17) 0.0404 (15) 0.0014 (13) 0.0052 (12) 0.0077 (14)C11 0.0484 (18) 0.046 (2) 0.0548 (18) 0.0029 (15) −0.0038 (14) 0.0102 (16)C12 0.080 (2) 0.054 (2) 0.078 (2) 0.0237 (19) 0.000 (2) 0.016 (2)C13 0.077 (3) 0.064 (3) 0.066 (2) 0.021 (2) 0.0135 (19) −0.010 (2)C14 0.077 (2) 0.057 (2) 0.0482 (18) 0.0014 (19) 0.0166 (16) 0.0025 (18)C15 0.066 (2) 0.0400 (19) 0.0446 (16) 0.0025 (15) 0.0129 (14) 0.0072 (15)C16 0.081 (2) 0.056 (2) 0.074 (2) 0.0041 (19) −0.0089 (19) 0.0300 (19)C17 0.072 (2) 0.107 (3) 0.075 (2) 0.029 (2) 0.0098 (19) 0.053 (2)C18 0.062 (2) 0.092 (3) 0.070 (2) 0.025 (2) −0.0013 (18) 0.019 (2)C19 0.0437 (16) 0.0451 (18) 0.0315 (14) 0.0013 (14) 0.0030 (12) 0.0125 (14)C20 0.0566 (18) 0.0373 (17) 0.0318 (13) 0.0053 (14) 0.0062 (13) 0.0115 (13)C21 0.075 (2) 0.044 (2) 0.0341 (15) −0.0026 (16) −0.0017 (14) 0.0108 (15)C22 0.121 (3) 0.054 (2) 0.0358 (16) 0.002 (2) 0.0013 (19) 0.0018 (17)C23 0.135 (4) 0.059 (3) 0.060 (2) 0.041 (3) 0.021 (2) 0.010 (2)C24 0.102 (3) 0.076 (3) 0.078 (3) 0.046 (2) 0.006 (2) 0.015 (2)C25 0.081 (2) 0.065 (2) 0.0493 (18) 0.025 (2) −0.0042 (17) 0.0100 (18)C26 0.093 (3) 0.069 (3) 0.062 (2) −0.007 (2) −0.032 (2) 0.009 (2)C27 0.055 (2) 0.0388 (18) 0.0419 (15) 0.0107 (15) 0.0153 (14) 0.0109 (14)C28 0.0520 (19) 0.0368 (18) 0.0594 (18) 0.0067 (15) 0.0205 (15) 0.0165 (16)C29 0.055 (2) 0.052 (2) 0.078 (2) 0.0041 (17) 0.0145 (18) 0.0153 (19)C30 0.061 (2) 0.074 (3) 0.124 (4) −0.011 (2) 0.016 (2) 0.028 (3)C31 0.084 (3) 0.073 (3) 0.140 (4) −0.006 (2) 0.045 (3) 0.042 (3)C32 0.103 (3) 0.076 (3) 0.098 (3) 0.008 (3) 0.040 (3) 0.049 (3)C33 0.071 (2) 0.065 (2) 0.079 (2) 0.0077 (19) 0.0254 (19) 0.036 (2)C34 0.082 (3) 0.107 (4) 0.084 (3) −0.014 (2) −0.011 (2) 0.025 (3)

Geometric parameters (Å, º)

Cu1—O1 1.961 (2) C23—C24 1.374 (6)Cu1—O3 1.9681 (19) C24—C25 1.374 (5)Cu1—O5 2.149 (2) C27—C28 1.497 (5)Cu1—O7 1.9871 (19) C28—C33 1.386 (5)Cu1—O9 1.943 (2) C28—C29 1.398 (5)Cu1—Cu2 2.5912 (4) C29—C34 1.503 (6)Cu2—O2 1.9896 (19) C29—C30 1.384 (5)Cu2—O4 1.9468 (19) C30—C31 1.364 (7)Cu2—O6 2.1358 (19) C31—C32 1.369 (6)Cu2—O8 1.9582 (18) C32—C33 1.380 (6)Cu2—O10 1.959 (2) C4—H4 0.9300O1—C1 1.259 (4) C5—H5 0.9300



O2—C1 1.272 (3) C6—H6 0.9300O3—C9 1.263 (3) C7—H7 0.9300O4—C9 1.261 (4) C8—H8A 0.9600O5—C17 1.411 (4) C8—H8B 0.9600O6—C18 1.405 (4) C8—H8C 0.9600O7—C19 1.267 (4) C12—H12 0.9300O8—C19 1.268 (3) C13—H13 0.9300O9—C27 1.260 (4) C14—H14 0.9300O10—C27 1.266 (4) C15—H15 0.9300O5—H5A 0.70 (3) C16—H16A 0.9600O6—H6A 0.72 (3) C16—H16B 0.9600C1—C2 1.490 (5) C16—H16C 0.9600C2—C7 1.396 (5) C17—H17A 0.9600C2—C3 1.386 (5) C17—H17B 0.9600C3—C4 1.413 (6) C17—H17C 0.9600C3—C8 1.496 (6) C18—H18A 0.9600C4—C5 1.351 (7) C18—H18B 0.9600C5—C6 1.351 (6) C18—H18C 0.9600C6—C7 1.378 (5) C22—H22 0.9300C9—C10 1.499 (4) C23—H23 0.9300C10—C11 1.400 (5) C24—H24 0.9300C10—C15 1.380 (4) C25—H25 0.9300C11—C16 1.515 (4) C26—H26A 0.9600C11—C12 1.385 (5) C26—H26B 0.9600C12—C13 1.375 (6) C26—H26C 0.9600C13—C14 1.363 (5) C30—H30 0.9300C14—C15 1.375 (4) C31—H31 0.9300C19—C20 1.493 (4) C32—H32 0.9300C20—C25 1.381 (5) C33—H33 0.9300C20—C21 1.394 (4) C34—H34A 0.9600C21—C26 1.504 (5) C34—H34B 0.9600C21—C22 1.386 (5) C34—H34C 0.9600C22—C23 1.358 (6)

Cu1···O2 3.0610 (19) C2···C18ii 3.466 (5)Cu1···O4 3.1243 (16) C6···C34ii 3.598 (6)Cu1···O8 3.102 (2) C8···O1 2.859 (4)Cu1···O10 3.0880 (18) C9···C1 3.555 (4)Cu1···O5i 3.849 (2) C11···C11iii 3.598 (5)Cu2···O7 3.0911 (16) C15···C18ii 3.561 (5)Cu2···O1 3.1299 (18) C15···O6ii 3.336 (4)Cu2···O3 3.049 (2) C16···O3 2.905 (4)Cu2···O9 3.078 (2) C17···O7i 3.405 (4)Cu1···H5Ai 3.20 (3) C17···C31iv 3.589 (6)Cu2···H6Aii 3.53 (3) C18···C15ii 3.561 (5)Cu2···H15ii 3.5900 C18···C2ii 3.466 (5)O1···Cu2 3.1299 (18) C19···C1 3.507 (4)O1···O3 2.765 (3) C26···O7 2.921 (4)



O1···O5 3.008 (3) C31···C17v 3.589 (6)O1···O7 2.731 (3) C34···O10 2.834 (4)O1···C8 2.859 (4) C34···C6ii 3.598 (6)O1···C19 3.183 (3) C1···H6Aii 2.80 (3)O2···C9 3.124 (3) C1···H8B 2.8400O2···O4 2.741 (3) C2···H18Aii 3.0100O2···Cu1 3.0610 (19) C2···H6Aii 3.01 (3)O2···O3 3.202 (3) C2···H23vi 2.9100O2···O6 3.067 (3) C4···H18Biv 2.8400O2···O8 2.758 (2) C4···H25iv 2.9300O2···O6ii 2.812 (2) C6···H34Cii 3.0100O3···C1 3.190 (4) C7···H23vi 2.9000O3···O9 2.800 (3) C7···H6Aii 3.08 (3)O3···Cu2 3.049 (2) C9···H16C 2.7800O3···C16 2.905 (4) C12···H16Ciii 3.0400O3···O5 3.055 (2) C13···H16Ciii 2.9600O3···O1 2.765 (3) C19···H5Ai 3.04 (3)O3···O2 3.202 (3) C19···H26C 2.7100O3···C17 3.331 (4) C25···H4v 2.9600O4···O6 2.930 (3) C26···H33i 3.0900O4···C27 3.262 (3) C27···H34C 2.8500O4···O2 2.741 (3) C28···H13iii 2.9600O4···Cu1 3.1243 (16) C29···H13iii 3.0700O4···O10 2.793 (2) C31···H17Cv 3.0600O5···Cu1i 3.849 (2) H4···C25iv 2.9600O5···O7i 2.793 (3) H4···H8C 2.3300O5···O7 3.118 (3) H4···H18Biv 2.3900O5···O9 3.049 (3) H4···H25iv 2.0900O5···O3 3.055 (2) H5A···Cu1i 3.20 (3)O5···O1 3.008 (3) H5A···O7i 2.11 (3)O6···O4 2.930 (3) H5A···C19i 3.04 (3)O6···C15ii 3.336 (4) H6···H16Avii 2.5100O6···O2ii 2.812 (2) H6A···Cu2ii 3.53 (3)O6···O2 3.067 (3) H6A···O2ii 2.10 (3)O6···O8 3.087 (2) H6A···C1ii 2.80 (3)O6···O10 3.070 (3) H6A···C2ii 3.01 (3)O7···O5i 2.793 (3) H6A···C7ii 3.08 (3)O7···O1 2.731 (3) H7···O2 2.5100O7···Cu2 3.0911 (16) H8A···O1 2.6100O7···C27 3.229 (4) H8B···O1 2.6700O7···C26 2.921 (4) H8B···C1 2.8400O7···C17i 3.405 (4) H8C···H4 2.3300O7···O9 2.760 (3) H12···H16A 2.3600O7···O5 3.118 (3) H13···C28iii 2.9600O8···C1 3.191 (4) H13···C29iii 3.0700O8···O6 3.087 (2) H15···O4 2.5400O8···O2 2.758 (2) H15···Cu2ii 3.5900O8···O10 2.764 (3) H15···O6ii 2.6300



O8···Cu1 3.102 (2) H16A···H6viii 2.5100O9···O7 2.760 (3) H16A···H12 2.3600O9···Cu2 3.078 (2) H16B···O3 2.7200O9···O5 3.049 (3) H16B···H30iv 2.4200O9···C9 3.299 (3) H16C···O3 2.6600O9···O3 2.800 (3) H16C···C9 2.7800O10···C18 3.414 (4) H16C···C12iii 3.0400O10···O4 2.793 (2) H16C···C13iii 2.9600O10···Cu1 3.0880 (18) H17C···C31iv 3.0600O10···C19 3.244 (4) H18A···C2ii 3.0100O10···C34 2.834 (4) H18B···C4v 2.8400O10···O8 2.764 (3) H18B···H4v 2.3900O10···O6 3.070 (3) H22···H26A 2.3900O1···H8A 2.6100 H23···C2vi 2.9100O1···H8B 2.6700 H23···C7vi 2.9000O2···H7 2.5100 H25···O8 2.4800O2···H6Aii 2.10 (3) H25···C4v 2.9300O3···H16C 2.6600 H25···H4v 2.0900O3···H16B 2.7200 H26A···H22 2.3900O4···H6A 2.89 (4) H26B···O7 2.9100O4···H15 2.5400 H26B···O9i 2.7700O6···H15ii 2.6300 H26C···O7 2.5000O7···H5Ai 2.11 (3) H26C···C19 2.7100O7···H26C 2.5000 H30···H16Bv 2.4200O7···H26B 2.9100 H30···H34A 2.2700O8···H25 2.4800 H33···O9 2.4600O9···H33 2.4600 H33···C26i 3.0900O9···H26Bi 2.7700 H34A···H30 2.2700O10···H34B 2.6900 H34B···O10 2.6900O10···H34C 2.5300 H34C···O10 2.5300C1···C9 3.555 (4) H34C···C27 2.8500C1···C19 3.507 (4) H34C···C6ii 3.0100

O1—Cu1—O3 89.46 (8) C29—C28—C33 119.7 (3)O1—Cu1—O5 93.97 (8) C27—C28—C29 123.1 (3)O1—Cu1—O7 87.51 (8) C28—C29—C30 117.6 (3)O1—Cu1—O9 169.65 (8) C28—C29—C34 124.5 (3)O3—Cu1—O5 95.69 (8) C30—C29—C34 117.9 (3)O3—Cu1—O7 166.39 (8) C29—C30—C31 122.7 (4)O3—Cu1—O9 91.44 (8) C30—C31—C32 119.4 (4)O5—Cu1—O7 97.76 (8) C31—C32—C33 120.0 (4)O5—Cu1—O9 96.20 (9) C28—C33—C32 120.6 (3)O7—Cu1—O9 89.21 (8) C3—C4—H4 119.00O2—Cu2—O4 88.25 (8) C5—C4—H4 119.00O2—Cu2—O6 95.98 (8) C4—C5—H5 119.00O2—Cu2—O8 88.61 (8) C6—C5—H5 119.00O2—Cu2—O10 166.98 (8) C5—C6—H6 120.00O4—Cu2—O6 91.63 (8) C7—C6—H6 120.00



O4—Cu2—O8 170.33 (7) C2—C7—H7 120.00O4—Cu2—O10 91.27 (8) C6—C7—H7 120.00O6—Cu2—O8 97.79 (8) C3—C8—H8A 109.00O6—Cu2—O10 97.04 (8) C3—C8—H8B 109.00O8—Cu2—O10 89.73 (8) C3—C8—H8C 109.00Cu1—O1—C1 120.95 (19) H8A—C8—H8B 109.00Cu2—O2—C1 122.11 (18) H8A—C8—H8C 109.00Cu1—O3—C9 123.09 (19) H8B—C8—H8C 109.00Cu2—O4—C9 120.24 (16) C11—C12—H12 119.00Cu1—O5—C17 123.77 (19) C13—C12—H12 119.00Cu2—O6—C18 127.16 (19) C12—C13—H13 120.00Cu1—O7—C19 121.75 (15) C14—C13—H13 120.00Cu2—O8—C19 122.5 (2) C13—C14—H14 121.00Cu1—O9—C27 122.8 (2) C15—C14—H14 121.00Cu2—O10—C27 121.48 (19) C10—C15—H15 119.00C17—O5—H5A 109 (3) C14—C15—H15 119.00Cu1—O5—H5A 125 (3) C11—C16—H16A 110.00Cu2—O6—H6A 115 (3) C11—C16—H16B 110.00C18—O6—H6A 113 (3) C11—C16—H16C 109.00O1—C1—O2 124.7 (3) H16A—C16—H16B 109.00O1—C1—C2 118.9 (3) H16A—C16—H16C 109.00O2—C1—C2 116.4 (3) H16B—C16—H16C 109.00C1—C2—C7 117.2 (3) O5—C17—H17A 110.00C3—C2—C7 119.9 (3) O5—C17—H17B 109.00C1—C2—C3 122.9 (3) O5—C17—H17C 109.00C4—C3—C8 119.4 (3) H17A—C17—H17B 109.00C2—C3—C4 117.1 (3) H17A—C17—H17C 110.00C2—C3—C8 123.4 (3) H17B—C17—H17C 109.00C3—C4—C5 121.7 (3) O6—C18—H18A 109.00C4—C5—C6 121.1 (4) O6—C18—H18B 109.00C5—C6—C7 119.4 (4) O6—C18—H18C 109.00C2—C7—C6 120.7 (3) H18A—C18—H18B 109.00O3—C9—O4 125.0 (2) H18A—C18—H18C 109.00O3—C9—C10 118.0 (3) H18B—C18—H18C 109.00O4—C9—C10 116.9 (2) C21—C22—H22 118.00C9—C10—C11 122.2 (2) C23—C22—H22 118.00C11—C10—C15 120.3 (3) C22—C23—H23 120.00C9—C10—C15 117.5 (3) C24—C23—H23 120.00C10—C11—C12 116.7 (3) C23—C24—H24 121.00C10—C11—C16 123.1 (3) C25—C24—H24 121.00C12—C11—C16 120.1 (3) C20—C25—H25 119.00C11—C12—C13 122.3 (4) C24—C25—H25 119.00C12—C13—C14 120.3 (3) C21—C26—H26A 109.00C13—C14—C15 118.8 (3) C21—C26—H26B 109.00C10—C15—C14 121.5 (3) C21—C26—H26C 109.00O7—C19—C20 119.7 (2) H26A—C26—H26B 109.00O8—C19—C20 116.2 (3) H26A—C26—H26C 109.00O7—C19—O8 124.1 (3) H26B—C26—H26C 109.00



C19—C20—C21 123.8 (3) C29—C30—H30 119.00C19—C20—C25 116.6 (2) C31—C30—H30 119.00C21—C20—C25 119.6 (3) C30—C31—H31 120.00C20—C21—C22 116.9 (3) C32—C31—H31 120.00C22—C21—C26 120.0 (3) C31—C32—H32 120.00C20—C21—C26 123.0 (3) C33—C32—H32 120.00C21—C22—C23 123.3 (3) C28—C33—H33 120.00C22—C23—C24 119.7 (4) C32—C33—H33 120.00C23—C24—C25 118.5 (4) C29—C34—H34A 109.00C20—C25—C24 122.1 (3) C29—C34—H34B 109.00O10—C27—C28 118.9 (3) C29—C34—H34C 109.00O9—C27—O10 124.5 (3) H34A—C34—H34B 109.00O9—C27—C28 116.7 (3) H34A—C34—H34C 109.00C27—C28—C33 117.2 (3) H34B—C34—H34C 109.00

O3—Cu1—O1—C1 −68.3 (2) C7—C2—C3—C4 0.4 (4)O5—Cu1—O1—C1 −164.0 (2) C7—C2—C3—C8 176.4 (3)O7—Cu1—O1—C1 98.4 (2) C1—C2—C7—C6 −178.9 (3)O1—Cu1—O3—C9 98.7 (2) C3—C2—C7—C6 1.5 (4)O5—Cu1—O3—C9 −167.4 (2) C2—C3—C4—C5 −1.6 (5)O9—Cu1—O3—C9 −71.0 (2) C8—C3—C4—C5 −177.7 (4)O1—Cu1—O5—C17 57.9 (3) C3—C4—C5—C6 0.8 (6)O3—Cu1—O5—C17 −31.9 (3) C4—C5—C6—C7 1.1 (6)O7—Cu1—O5—C17 146.0 (3) C5—C6—C7—C2 −2.3 (5)O9—Cu1—O5—C17 −124.0 (3) O3—C9—C10—C11 −39.6 (4)O1—Cu1—O7—C19 −69.7 (2) O3—C9—C10—C15 139.8 (3)O5—Cu1—O7—C19 −163.4 (2) O4—C9—C10—C11 143.2 (3)O9—Cu1—O7—C19 100.5 (2) O4—C9—C10—C15 −37.4 (4)O3—Cu1—O9—C27 95.7 (2) C9—C10—C11—C12 178.1 (3)O5—Cu1—O9—C27 −168.4 (2) C9—C10—C11—C16 −5.0 (4)O7—Cu1—O9—C27 −70.7 (2) C15—C10—C11—C12 −1.3 (4)O4—Cu2—O2—C1 104.1 (2) C15—C10—C11—C16 175.6 (3)O6—Cu2—O2—C1 −164.4 (2) C9—C10—C15—C14 −176.3 (3)O8—Cu2—O2—C1 −66.7 (2) C11—C10—C15—C14 3.1 (5)O2—Cu2—O4—C9 −66.4 (2) C10—C11—C12—C13 −1.6 (5)O6—Cu2—O4—C9 −162.3 (2) C16—C11—C12—C13 −178.6 (3)O10—Cu2—O4—C9 100.6 (2) C11—C12—C13—C14 2.7 (5)O2—Cu2—O6—C18 150.2 (3) C12—C13—C14—C15 −0.8 (5)O4—Cu2—O6—C18 −121.4 (3) C13—C14—C15—C10 −2.0 (5)O8—Cu2—O6—C18 60.8 (3) O7—C19—C20—C21 −35.8 (5)O10—Cu2—O6—C18 −30.0 (3) O7—C19—C20—C25 143.3 (3)O2—Cu2—O8—C19 96.3 (2) O8—C19—C20—C21 146.1 (3)O6—Cu2—O8—C19 −167.91 (19) O8—C19—C20—C25 −34.8 (4)O10—Cu2—O8—C19 −70.8 (2) C19—C20—C21—C22 179.2 (3)O4—Cu2—O10—C27 −70.4 (2) C19—C20—C21—C26 −2.8 (5)O6—Cu2—O10—C27 −162.2 (2) C25—C20—C21—C22 0.2 (5)O8—Cu2—O10—C27 100.0 (2) C25—C20—C21—C26 178.2 (3)Cu1—O1—C1—O2 −5.1 (4) C19—C20—C25—C24 −178.1 (3)



Cu1—O1—C1—C2 175.2 (2) C21—C20—C25—C24 1.0 (5)Cu2—O2—C1—O1 −13.4 (4) C20—C21—C22—C23 −1.1 (6)Cu2—O2—C1—C2 166.3 (2) C26—C21—C22—C23 −179.1 (4)Cu1—O3—C9—O4 −4.6 (4) C21—C22—C23—C24 0.8 (6)Cu1—O3—C9—C10 178.5 (2) C22—C23—C24—C25 0.5 (6)Cu2—O4—C9—O3 −12.2 (4) C23—C24—C25—C20 −1.3 (6)Cu2—O4—C9—C10 164.7 (2) O9—C27—C28—C29 152.6 (3)Cu1—O7—C19—O8 −11.6 (4) O9—C27—C28—C33 −26.3 (4)Cu1—O7—C19—C20 170.5 (2) O10—C27—C28—C29 −27.7 (5)Cu2—O8—C19—O7 −5.2 (4) O10—C27—C28—C33 153.3 (3)Cu2—O8—C19—C20 172.75 (19) C27—C28—C29—C30 −177.4 (3)Cu1—O9—C27—O10 −5.8 (4) C27—C28—C29—C34 0.3 (6)Cu1—O9—C27—C28 173.90 (19) C33—C28—C29—C30 1.5 (5)Cu2—O10—C27—O9 −10.5 (4) C33—C28—C29—C34 179.2 (4)Cu2—O10—C27—C28 169.8 (2) C27—C28—C33—C32 178.6 (4)O1—C1—C2—C3 −34.3 (4) C29—C28—C33—C32 −0.4 (6)O1—C1—C2—C7 146.2 (3) C28—C29—C30—C31 −1.2 (6)O2—C1—C2—C3 146.0 (3) C34—C29—C30—C31 −179.1 (4)O2—C1—C2—C7 −33.6 (4) C29—C30—C31—C32 −0.1 (7)C1—C2—C3—C4 −179.2 (3) C30—C31—C32—C33 1.3 (7)C1—C2—C3—C8 −3.2 (4) C31—C32—C33—C28 −1.0 (7)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) x+1, y, z; (vi) −x+1, −y−1, −z; (vii) x, y−1, z; (viii) x, y+1, z.

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of C2–C7 and C28–C33 rings, respectively.

D—H···A D—H H···A D···A D—H···A

O5—H5A···O7i 0.70 (3) 2.11 (3) 2.793 (3) 167 (4)O6—H6A···O2ii 0.72 (3) 2.10 (3) 2.812 (2) 174 (4)C18—H18A···Cg1ii 0.96 2.98 3.749 (4) 137.00C23—H23···Cg1vi 0.93 2.87 3.735 (4) 154.00C13—H13···Cg2iii 0.93 2.97 3.877 (4) 165.00

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (vi) −x+1, −y−1, −z.

Download - metal-organic compoundsjournals.iucr.org/e/issues/2010/05/00/bq2206/bq2206.pdf · Muhammad Danish, Iram Saleem, M. Nawaz Tahir, Nazir Ahmad and Abdur Rauf Raza S1. Comment In continuation

Top Related